Synthesis and Anti-Tuberculosis Activity of the Marine Natural Product Caulerpin and Its Analogues

• Main Authors: Cristina I. Canché Chay, Rocío Gómez Cansino, Clara I. Espitia Pinzón, Rubén O. Torres-Ochoa, Roberto Martínez
• Format: Article
• Language: English
• Published: MDPI AG 2014-03-01
• Series: Marine Drugs
• Subjects: synthesis; caulerpin; analogues; anti-tuberculosis activity
• Online Access: http://www.mdpi.com/1660-3397/12/4/1757

Caulerpin (1a), a bis-indole alkaloid from the marine algal Caulerpa sp., was synthesized in three reaction steps with an overall yield of 11%. The caulerpin analogues (1b–1g) were prepared using the same synthetic pathway with overall yields between 3% and 8%. The key reaction involved a radical oxidative aromatic substitution involving xanthate (3) and 3-formylindole compounds (4a–4g). All bis-indole compounds synthesized were evaluated against the Mycobacterium tuberculosis strain H37Rv, and 1a was found to display excellent activity (IC50 0.24 µM).